Piperazine → 3-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6,8-difluoro-4-oxo-7-(1-piperazinyl)-

HRID 979468Notes

Reaction equation

HRID 979468 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.C(N(CC)CC)C>C(#N)C>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 8471TriethylamineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 30663963-Quinolinecarboxylic acid, 1,4-dihydro-5-amino-1-cyclopropyl-6,8-difluoro-4-oxo-7-(1-piperazinyl)-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 1.0 g (3.35 mmole) of 5-amino-1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, 1.15 g (13.4 mmole) of piperazine, 1.36 g (13.35 mmole) of triethylamine and 60 ml of acetonitrile is refluxed for three hours and then stirred at room temperature for 16 hours. The precipitate is removed by filtration, washed with acetonitrile and dried in vacuo at 60° C. to give 5-amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid, mp 257°-259° C.

Workup

  1. temperatureis refluxed for three hours
  2. customThe precipitate is removed by filtration
  3. washwashed with acetonitrile
  4. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-4e3277fa31994f43858a590d0adf1231
Source dataset
uspto-grants-1987_05
Patent number
US04668680

Reaction notes

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